A Manhattan Supreme Court lawsuit says Marianne Flippo was defrauded out of nearly $6 million after trying to keep a man she met through Cowboys 4 Angels in an exclusive arrangement.
The filing names Gregg Starr and the agency Cowboys 4 Angels and says Flippo paid roughly $635,000 for eight months of exclusive companionship before being told the only way to make the arrangement permanent was to pay $10 million to buy Starr out of his contract.
Flippo said in a sworn affirmation that she 'now recognize[s] that I was the victim of a horrendous scheme by Starr who is a sociopath who lacks any conscience.' The lawsuit says she was newly widowed, managing money alone for the first time, and living with a rare genetic disorder that increased her vulnerability to drugs and alcohol.
Court papers allege that in February 2026, two agency employees showed up unannounced during a trip to visit Starr’s mother and pressed her to drink at lunch despite knowing she was on medication for a recent surgery. After roughly five drinks, they produced an 'Exit Agreement' requiring her to pay $10 million to end Starr’s ties to the agency.
Flippo said she was 'drunk and confused' and was taken to a hotel room before signing a document she says she had never seen earlier that day. The agreement states that 'under no circumstances has physical companionship been purchased for consideration.'
According to the filing, her attempts to wire the $10 million were flagged as suspected fraud by JPMorgan Chase and later by Westpac. Starr then directed her to open a joint account at Charles Schwab, which she says allowed him access without triggering a bank fraud review.
The lawsuit says she transferred $5.95 million into that account, and bank records filed with the court show Starr moved $5,719,010.37 into an account in his name alone within weeks, leaving the balance at $12.61 by the end of June.
The filing also says Flippo paid the agency $27,000 for Starr’s assistance in three $9,000 payments and later agreed to pay roughly $150,000 for Starr to be 'exclusive' with her. By December 1, 2025, Starr had moved into her Upper West Side apartment, and she signed a formal 'Independent Contractor Agreement' paying $368,000 for companionship through May.
Chad, Flippo’s late husband, joined Roblox when it was still a startup and helped build what Flippo described as 'a substantial amount of wealth.' He died by suicide in August 2024 after battling depression, according to the filing.
The numbers come first. This case is not just about one widow’s loss; it is about how quickly large sums can be drained when trust, dependency and loose controls collide. Capital rewards clear rules, and the paper trail in this lawsuit suggests those rules were either ignored or gamed.
For readers, the broader lesson is plain: private wealth still needs guardrails. When fraud claims land in court, the market has already voted on the cost of weak oversight. The taxpayer should not have to clean up the wreckage of bad contracts and bad incentives.
